ornidazole

{{Short description|Chemical compound}}

{{Distinguish|ronidazole}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 447378516

| drug_name =

| type =

| IUPAC_name = 1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol

| image = Ornidazole.svg

| alt =

| caption =

| tradename = Xynor

| Drugs.com = {{drugs.com|international|ornidazole}}

| MedlinePlus =

| licence_EU =

| licence_US =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_status =

| routes_of_administration = Oral

| bioavailability =

| metabolism = Via liver{{Rp|1356}}

| elimination_half-life = 12-13 hours{{Rp|1356}}

| excretion = Urine (63%) and Feces (22%)

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 16773-42-5

| ATC_prefix = G01

| ATC_suffix = AF06

| ATC_supplemental = {{ATC|J01|XD03}} {{ATC|P01|AB03}} {{ATCvet|P51|AA03}}

| PubChem = 28061

| DrugBank = DB13026

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 26102

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1449676

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 62XCK0G93T

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D05274

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 75176

| C = 7

| H = 10

| Cl = 1

| N = 3

| O = 3

| smiles = [O-] [N+](=O)c1cnc(n1CC(O)CCl)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C7H10ClN3O3/c1-5-9-3-7(11(13)14)10(5)4-6(12)2-8/h3,6,12H,2,4H2,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = IPWKIXLWTCNBKN-UHFFFAOYSA-N

}}

Ornidazole is an antibiotic used to treat protozoan infections.{{cite book | vauthors = Kuhlmann FM, Fleckenstein JM | chapter = 157 - Antiparasitic Agents|date=2017-01-01|chapter-url=http://www.sciencedirect.com/science/article/pii/B978070206285800157X | veditors = Cohen J, Powderly WG, Opal SM |title =Infectious Diseases | edition = Fourth |pages=1345–1372.e2 |publisher=Elsevier| doi = 10.1016/B978-0-7020-6285-8.00157-X|isbn=978-0-7020-6285-8 }}{{Rp|1368}} A synthetic nitroimidazole, it is commercially obtained from an acid-catalyzed reaction between 2-methyl-5-nitroimidazole and epichlorohydrin. {{cite book | name-list-style = vanc | vauthors = Sharma S, Anand N | chapter = Chapter 17 - Nitroheterocycles |date= January 1997 | title = Pharmacochemistry Library |volume=25 |pages=428 | veditors = Sharma S, Anand N|series=Approaches to Design and Synthesis of Antiparasitic Drugs |publisher=Elsevier |doi=10.1016/S0165-7208(97)80039-6 |isbn=9780444894762 }} Ornidazole is nothing but chloro-secnidazole.

Antimicrobial spectrum is similar to that of metronidazole and is more well tolerated;{{Rp|1368}} however there are concerns of lower relative efficacy.{{cite book | vauthors = Nagel JL, Aronoff DM | chapter = 28 - Metronidazole|date= January 2015 | veditors = Bennett JE, Dolin R, Blaser MJ | title = Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases | edition = Eighth |pages=356 |publisher=Content Repository Only!|isbn=978-1-4557-4801-3 }}

It was first introduced for treating trichomoniasis before being recognized for its broad anti-protozoan and anti-anaerobic-bacterial capacities.{{Citation| vauthors = Wilcox MH | chapter = 147 - Nitroimidazoles, Metronidazole, Ornidazole and Tinidazole; and Fidaxomicin |date= January 2017 | veditors = Cohen J, Powderly WG, Opal SM | title = Infectious Diseases | edition = Fourth |pages=1261–1263.e1 |publisher=Elsevier|isbn=978-0-7020-6285-8 }}{{Rp|1261}} has also been investigated for use in Crohn's disease after bowel resection.{{cite journal | vauthors = Rutgeerts P, Van Assche G, Vermeire S, D'Haens G, Baert F, Noman M, Aerden I, De Hertogh G, Geboes K, Hiele M, D'Hoore A, Penninckx F | display-authors = 6 | title = Ornidazole for prophylaxis of postoperative Crohn's disease recurrence: a randomized, double-blind, placebo-controlled trial | journal = Gastroenterology | volume = 128 | issue = 4 | pages = 856–861 | date = April 2005 | pmid = 15825069 | doi = 10.1053/j.gastro.2005.01.010 | doi-access = free }}